6-Fluoro-1-(4-fluoro-phenyl)-4-oxo-7-(3-oxo-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid | 98106-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-Fluoro-1-(4-fluoro-phenyl)-4-oxo-7-(3-oxo-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 6-Fluoro-1-(4-fluorophenyl)-4-oxo-7-(3-oxopiperazin-1-yl)quinoline-3-carboxylic acid
• CAS: 98106-45-7
• 化学式: C₂₀H₁₅F₂N₃O₄
• 分子量: 399.354
• InChiKey: VXJGEYCLYRSZFR-UHFFFAOYSA-N

物化性质

• 熔点：
  >275 °C
• 沸点：
  713.1±60.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(2,4-二氯-5-氟苯甲酰基)-3-乙氧基丙烯酸乙酯 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 6-Fluoro-1-(4-fluoro-phenyl)-4-oxo-7-(3-oxo-piperazin-1-yl)-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents

  摘要：

  A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.

  DOI：

  10.1021/jm00149a003

文献信息

• CHU, D. T. W.;FERNANDES, P. B.;CLAIBORNE, A. K.;PIHULEAC, E.;NRDEEN, C. W+, J. MED. CHEM., 1985, 28, N 11, 1558-1564
  作者：CHU, D. T. W.、FERNANDES, P. B.、CLAIBORNE, A. K.、PIHULEAC, E.、NRDEEN, C. W+

  DOI：——

  日期：——
• Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents
  作者：Daniel T. W. Chu、Prabhavathi B. Fernandes、Akiyo K. Claiborne、Eva Pihuleac、Carl W. Nordeen、Robert E. Maleczka、Andre G. Pernet

  DOI：10.1021/jm00149a003

  日期：1985.11

  A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.